Melamine → 2-{2-[(4,6-Diamino-1,3,5-triazin-2-yl)amino]ethoxy}ethan-1-ol

HRID 381664Notes

Reaction equation

HRID 381664 reaction equation
[N:1]1[C:8]([NH2:9])=[N:7][C:5]([NH2:6])=[N:4][C:2]=1[NH2:3].[H][H].[CH2:12]([OH:18])[CH2:13][O:14][CH2:15][CH2:16]O>[Pd]>[NH2:3][C:2]1[N:4]=[C:5]([NH2:6])[N:7]=[C:8]([NH:9][CH2:16][CH2:15][O:14][CH2:13][CH2:12][OH:18])[N:1]=1

Participants

5

Reactant 3

HCID 7955Melamine2×HCID 8117Diethylene GlycolHCID 178418361HCID 178418361, compound

Product 1

HCID 155976522-{2-[(4,6-Diamino-1,3,5-triazin-2-yl)amino]ethoxy}ethan-1-olYield 13.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a stainless steel autoclave of an inner volume of 100 ml, 1.26 g (10 mmol) of melamine, 250 mg of 5% Pd—C catalyst, and 30 ml of diethylene glycol were charged. After the inside of the reaction system was sufficiently substituted with nitrogen gas, 10 kg/cm2 of hydrogen gas was introduced under pressure at normal temperature. Then, the temperature was elevated while stirring, and after the temperature reached 260° C., the reaction was carried out at the same temperature for further 2 hours. After cooling, the reaction mixture was taken out and quantitative analysis of the reaction product was performed under the above analytical conditions. As a result, the reaction conversion rate of the starting material melamine was 21.5% and it was confirmed that there was produced only 13.5% of 2,4-diamino-6-(5-hydroxy-3-oxapentylamino)-1,3,5-triazine as the product, and an obvious decrease in activity as compared with the mixed catalyst systems was confirmed.

Workup

  1. additionwas introduced under pressure at normal temperature
  2. customreached 260° C.
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-bcbd169979a94f11935968754088de9f
Source dataset
uspto-grants-2001_10
Patent number
US06307046B1

Reaction notes

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